Water-soluble dyestuff and process of producing same



Patented Sept. 11, 1928 UNITED STA TES PATENT orr cs orro srnnnrvr, F nn'ssn'o, KARL rnrrzss, or Hoonsr-oN rHn-MAIN, BERNHARD,

sorrorinn, or woman, NEAR nrr'rnnrnrn, ROBERT sonivrrnnrn', or sooner-0N- THE-MAIN, WALTHER BENAD'E, or DESSAU, AND BERNHARD nnroirn, or Hoorrsr- QN-THE-MAIN, GERMANY ASS IGNORS 'ro GRASSELLI nvnsrurn oonroanrron, on NEW YQRK, N. Y., A oon-ro'narron or nnLAwAn i.

WATER-SOLUBLE DYES'IUFF AND PROCESS OF ERODUCING SAME.

No Drawing. Application filed June 17, 1926, Serial Nor 116006, and in Germany May 5, 1923.

The present invention relates to watersoluble dyestuffs of the generaltormula:

Y Y i l general formula Hlg wherein X represents hydrogen or the sulfonie acid group, Z hydrogen or the nitro groupQand Hlg an exchangeable halogen. Our new compounds are similar to the watersoluble dyestufiis describedin the U. S. Patent 1059.571. However, they dye wool faster and more even tint-s than the dyestuffs described in the above-mentioned patent. They are also suitable for the dyeing of leather.

The following examples serve to illustrate our invention, all parts being by weight:

1 309 parts of 4-nitro- F-aminodiphenyl- :nnine-Q-sulfonic acid are-dissolved in 300 parts of water by'ad ding thereto sodium carbon'ate; there are then further added 8.2 parts of sodium acetate 15.7 parts of 2-nitro-1- chlorobenzene, so'r'n'e alcohol and very little copper bronze and the mixture is kept for several hours at the boiling point. The solution, which soon forms, assumesa deeper color. After having filtered hot, the new condensation product crystallizes out on cooling partly in the form of its sodium salt and on addition of common salt further separation talzes place. As free acid, the dyestufi constitutes a yellow crystalline powder and dyes wool in an acid bath neutral-yellow eminently even tints of thoroughly good :fast nessi fastness to light is excellent.

The dyestuff correspondswith the following H graphical formula:

V 2\ 1 1' a" I '4 2 4' 1 N0l, SOaH N02 I 2. By condensing according to the method laid down 111 Example 1 one molecule of 2- ni tro-4-am nodiphenylamine-4-sulfonic' acid with one molecule of 1-chloro:2 nitrobenzenelc-S11liOl11C acid, a dyestu'ff yielding a clear yellowish-brown tint of very good fastness to light, to *ashing and to the action'oi alkalies is produced corresponding with the followv in g graphical formula:

O/NHO 036311 SO3H/ NOz NH/ I N02 I 320 parts of potassium-1-chloro-2.6-cli nitrobenzone-t-sultonate (one molecule) are boiled for several hours in 3000 parts of water, with 26. 1 parts of 4-an1inodiphenyl amine-Qsulionic acid (one molecule) while adding the required 'quantity of sodium ac tate; The resulting roducts worked up as indicated in Example. 1. The dyestuif thus obtained forms a deepjlorown powder and dyes wool fast brown tints, which are re markable for their extremely good iastness to washing. The dyestuff corresponds with the following graphical formula:

' SOaH i l I V I ./NH\ no2 s our N Oz r 4. 28.6 parts of sodium-baminodiphenylamine-Q-sulfonate dissolved in 1000 parts of water are heated, while stirring, with 20.3 parts of 2.6-dinitro-1-chlorobenZene to 100 C- during which operation there are run in within 4 hours. 5.5 parts of sodium carbonate in form of a solution of 10% strength. The resulting solution is filtered While hot, the dyestufifatter being salted out separated by pressing and dried. It d es wool in an acid batha red-brown tint. T edyestufi corresponds with the following formula NHONO r NED I NO:

5. 18.4 parts of 4-aminodiphenylamine are dissolved together With 12 parts of concen trated hydrochloric acid in 400 parts of Water.

1 There then added a solution of 30.5 parts the followinggraphical formula:

N O NnUN0 son-r V V NH/ i N O: We claim:

1. As new products Water-soluble dyestuffs of the general formula:

V Y Y i Y- NH Y z x Y- Y Y Nu j i i Y Y NO;

wherein X represents hydrogen or the sulfonio acid group, Z' hydrogen or the nitro group, andY the hydrogen-, nitro-, alkyl-, or sulfonic acid group.

2. As new products water-soluble dyestuffs of the general formula: p

Y Y V Y NH7 Y 2 30th Y Y Y NH Y i i 1110:

After wherein Y represents hydrogen, nitro-, al-

kyl-, orsulfonic acid group, and Z hydrogen or the nitro oup.

3. As new pro ucts Water-soluble dyestufl's I of the general formula SOzH to, wherein Y represents hydrogennitro-,, alkyl-, or sulfonic acid group.

4. As new products Water-soluble dyestufis of the general formula:

' NH z x NH 7 V l V 1 10: J v

wherein X represents hydrogen or the sulfonic acid group, and Z hydrogen or the nitro group.

of the general formula wherein Z represents hydrogen or the nitro group.

6. As a new product a Water-soluble dyestuff of the general formula:

. NE N0 SOaH.

which dyes Wool reddish-brown shades from an acid bath. 7

In testimony whereof, we affix our signatures.

OTTO SIEBERT. KARL THIESS. BERNHARD SCHONER. ROBERT SCHMIDLIN. ,WALTHER BENADE. BERNHARD DEICKE.

5. As new products water-soluble dyestuffs 1 

